The 7 Best Side Characters in The Simpsons (Who Deserve Spin-Offs)

We all know who the main characters are in The Simpsons. But when it comes to the side characters, who would you say are your favorites?

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For over thirty years now, The Simpsons has been part of our lives and the series has grown to become a universally recognized and accepted part of modern culture as a whole.

The first ten seasons set the standard for comedy writing on TV—a benchmark that still holds to this day. All animated comedy shows that feature adult themes are in the shadow of The Simpsons, and most owe their existence to the ground that The Simpsons first broke.

We all know about the exploits of Homer, Marge, Bart, Lisa, and Maggie because the show’s focus has been on them for decades. But what if Disney were to order some spin-off series that follow the adventures of the expanded cast of The Simpsons more closely?

Here are our picks for the best side characters in The Simpsons and why they’d be well suited to lead a spin-off series.

7. Mrs. Krabappel

When Marcia Wallace passed away, The Simpsons lost one of its best characters: Bart’s long-standing nemesis and friend, Edna Krabappel. Her presence in the series was always a great one, as she consistently did battle with Bart even as the pair had mutual respect for one another.

A spin-off series that follows Edna Krabappel before she became a teacher at Springfield Elementary School might be an opportunity to get a deeper look at the character.

Her being a younger teacher at a different school—or even getting her teaching qualifications—would be a good starting point for Edna, as well as a chance for us all to see her again.

6. Milhouse Van Houten

Contrary to popular belief and what Mr. Largo says, everybody loves Milhouse. He’s Bart’s best friend and the kid at school who can’t seem to ever get it together.

However, he’s a lovable character and a good person at his core. His crush on Lisa often makes Lisa cringe, but in the future it’s known that Lisa did eventually have a relationship with Milhouse.

A spin-off with Milhouse would be tricky, but it could be done. A series that focuses on his time spent living with his Mom in Capitol City would be good, or maybe even a Lisa and Milhouse spin-off set in the future when they’re dating. Either way, it would be good to see!

5. Mr. Burns

The tyrannical Mr. Burns is one of Springfield’s grandest villains and most dominant forces in the series.

His ownership of the power plant—and therefore his stranglehold of the town—has been well documented over the show’s run. However, every show needs an opposing force, and Mr. Burns has so often been it.

A limited series that shows M.r Burns’ life before the events of The Simpsons would be fun. Or, if the showrunners were to be very bold, they could do a further parody of his comparisons to Charles Foster Kane and make the show about his death and what his life meant to other people.

4. Moe Szyslak

Moe is, pound for pound, one of hte most comedic characters in the series. His antics are always detrimental to him and often lead to him being more lonely and sad than before.

Generally, Moe is a borderline suicidal and angry man who hates his life, but beneath all that is great empathy and love for those around him.

A spin-off series with Moe in the lead could be set during his days at bartending school or during his first arrival as an immigrant. Moe is one of the show’s least understood characters, so getting to know him better after these 30 years would be interesting for fans.

3. Barney Gumble

Homer’s best friend and fellow astronaut (briefly), Barney Gumble is the town drunk who’s always at Moe’s.

The joke has been funny for a long while, but the series has made it clear that he knew he was beyond hope with his short film entry to Springfield’s film festival, turning Barney into more of a tragic character.

A series centred around Barney and his filmmaking prowess could be a brilliantly funny and intriguing show. Or a show that resurrects his Snow King business and helps out various Springfield residents in the winter.

2. Principal Skinner

If Edna Krabappel is Bart’s direct enemy, then Principal Skinner is his arch-foe. The pair have dueled wonderfully over the years, with both winning several times.

Further than that, Skinner has a past that the show wants you to forget about—because revealing him not to be the original Seymour Skinner was the moment the show began to jump the shark.

They should lean into this more now, with a show that focuses on his days as a street punk in Capitol City or his days spent in Vietnam. Both would be fantastic to see, plus we could see who his real parents were!

1. Ned Flanders

Ned Flanders is both the best and worst neighbor one could have. He’s a wonderful and kind man who would do anything for you—but Homer isn’t wrong to be annoyed by him, since living next door to somebody this perfect would drive anyone insane.

When Ned lost Maude, Homer did resolve to be a nicer neighbor to Ned, indicating he knows how badly he’s treated Ned over the years.

A series that focuses on Ned and Maude’s early years would be interesting, including how they met and how Ned’s dislike of his parents fostered resentment inside him.

Ned is repressed about many things, so seeing a more reckless Flanders could be the best spin-off series The Simpsons ever has.

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